:Levuglandin

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| ImageFile=Levuglandin D2.svg

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| IUPACName=(5Z,8R,9R,10E,12S)-9-acetyl-8-formyl-12- hydroxyheptadeca-5,10-dienoic acid

| Name=Levuglandin D₂

| OtherNames=

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=91712-44-6

| PubChem=9548876

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 7827799

| SMILES = CCCCC[C@@H](/C=C/[C@H]([C@@H](C/C=C\CCCC(=O)O)C=O)C(=O)C)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C20H32O5/c1-3-4-7-11-18(23)13-14-19(16(2)22)17(15-21)10-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = MLLWPVVMXGUOHD-QNUMDXCLSA-N

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG=C13808

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|Section2={{Chembox Properties

| Formula=C₂₀H₃₂O₅

| MolarMass=352.465 g/mol

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{{chembox

| ImageFile=Levuglandin E2.svg

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| IUPACName=(5Z,8R,9R,10E,12S)-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid

| Name=Levuglandin E₂

| OtherNames= LGE2

|Section1={{Chembox Identifiers

| CASNo=91712-41-3

| PubChem=5771742

| ChemSpiderID = 4696839

| SMILES = CCCCC[C@@H](/C=C/[C@@H](C=O)[C@@H](C/C=C\CCCC(=O)O)C(=O)C)O

| StdInChI = 1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1

| StdInChIKey = WJWAORNTZNRHBP-QNUMDXCLSA-N

| KEGG=C13807

}}

|Section2={{Chembox Properties

| Formula=C₂₀H₃₂O₅

| MolarMass=352.465 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

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Levuglandins are reactive aldehydes formed by the spontaneous rearrangement of prostaglandin H (PGH). Enantiomerically pure levuglandin (LG) E₂ can also be formed through the cyclooxygenase (COX) pathway by a rearrangement of the prostaglandin (PG) endoperoxide PGH ₂.{{cite journal |author=Salomon RG |title=Isolevuglandins, oxidatively truncated phospholipids, and atherosclerosis |journal=Ann. N. Y. Acad. Sci. |volume=1043 |pages=327–42 |year=2005 |issue=1 |pmid=16037255 |doi=10.1196/annals.1333.040|bibcode=2005NYASA1043..327S |s2cid=12782911 }} They are nonclassic eicosanoids. One species, levuglandin E₂, (LGE₂), forms neurotoxic adducts with

amyloid beta.{{cite journal

|doi = 10.1111/j.1471-4159.2005.03586.x|title = PGH2-derived levuglandin adducts increase the neurotoxicity of amyloid beta1-42|year = 2006|last1 = Boutaud|first1 = Olivier|last2 = Montine|first2 = Thomas J.|last3 = Chang|first3 = Lei|last4 = Klein|first4 = William L.|last5 = Oates|first5 = John A.|journal = Journal of Neurochemistry|volume = 96|issue = 4|pages = 917–923|pmid = 16412101|pmc = 1621054}}{{cite journal|doi=10.1021/bi990470+|pmid=10413514|year=1999|last1=Boutaud|first1=O.|last2=Brame|first2=C. J.|last3=Salomon|first3=R. G.|last4=Roberts Lj|first4=2nd|last5=Oates|first5=J. A.|title=Characterization of the lysyl adducts formed from prostaglandin H2 via the levuglandin pathway|journal=Biochemistry|volume=38|issue=29|pages=9389–96}}

Levuglandins and isolevuglandins can damage proteins by covalent adduction, thereby interfering with their normal functions.

These lipid-derived protein modifications may serve as dosimeters of oxidative injury.

Elevated plasma levels of isoLG-protein epitopes are associated with atherosclerosis but are independent of total cholesterol, a classical risk factor.